(E)-3-(3,4-dihydroxyphenyl)-N-methyl-N-phenylacrylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-dihydroxyphenyl)-N-methyl-N-phenylacrylamide
• 英文别名: 3,4-dihydroxy-trans-cinnamic acid-(N-methyl-anilide)；3,4-Dihydroxy-trans-zimtsaeure-(N-methyl-anilid)；(E)-3-(3,4-dihydroxyphenyl)-N-methyl-N-phenylprop-2-enamide
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: HYRSVUOIUALHGB-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯化亚砜 作用下， 生成 (E)-3-(3,4-dihydroxyphenyl)-N-methyl-N-phenylacrylamide
  参考文献：
  名称：

  Freudenberg; Fischer, Chemische Berichte, 1956, vol. 89, p. 1230,1231

  摘要：

  DOI：

文献信息

• Synthesis, structure and structure–activity relationship analysis of caffeic acid amides as potential antimicrobials
  作者：Jie Fu、Kui Cheng、Zhi-ming Zhang、Rui-qin Fang、Hai-liang Zhu

  DOI：10.1016/j.ejmech.2010.01.066

  日期：2010.6

  A series of caffeic acid amides 1-23 were synthesized and nine of which (13-17, 19-21 and 23) were reported for the first time. The chemical structures of these compounds were confirmed by means of H-1 NMR, ESI MS and elemental analyses. Compound 15 was determined by single-crystal X-ray diffraction analysis. All of the compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT method. Compounds 10-12, 15, 18 and 21 showed considerable antibacterial activities against B.subtilis with MICs of 795, 625, 389, 118, 312 and 155 mu g/mL, respectively. Structure-activity relationship analysts disclosed that caffeic acid amilides with electron-donating groups at p-position of benzene ring have better inhibitory activities.
• Freudenberg; Fischer, Chemische Berichte, 1956, vol. 89, p. 1230,1231
  作者：Freudenberg、Fischer

  DOI：——

  日期：——